Cesium carbonate → 1-[2,5-Bis(methyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine

HRID 1014212노트

반응식

HRID 1014212 반응식
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].[CH:15]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:14][O:13][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=1[N:21]1[CH2:22][CH2:23][N:18]([CH:15]([CH3:17])[CH3:16])[CH2:19][CH2:20]1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 780131-IsopropylpiperazineHCID 813621-Chloro-2,5-dimethoxy-4-nitrobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

생성물 1

HCID 594421271-[2,5-Bis(methyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine수율 76%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
100 °C

실험 절차

1-chloro-2,5-bis(methyloxy)-4-nitrobenzene (3.25 g, 15 mmol, TCl America), isopropylpiperizine (3.84 g, 30 mmol, Oakwood Products), cesium carbonate (9.8 g, 30 mmol), Pd2dba3 (1.37 g, 1.5 mmol), and XANTPHOS (1.3 g, 2.25 mmol) were added to degassed dioxane (80 mL) and heated to 100° C. under a water cooled reflux condenser for 12 hours. The dioxane was removed under reduced pressure and the solids were partitioned between methylene chloride (500 mL) and water (500 mL). The organic layer was dried over sodium sulfate, taken to a residue under reduced pressure, and purified by chromatography on SiO2to give 1-[2,5-bis(methyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine as a yellow solid (3.5 g, 11.3 mmol, 76% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.09 (d, J=6.60 Hz, 6 H), 2.69-2.73 (m, 4 H), 2.75 (d, J=6.60 Hz, 1 H), 3.23-3.32 (m, 4 H), 3.88 (s, 3 H), 3.94 (s, 3 H), 6.48 (s, 1 H), 7.55 (s, 1 H).

후처리

  1. customto degassed dioxane (80 mL)
  2. temperaturecooled
  3. temperaturereflux condenser for 12 hours
  4. customThe dioxane was removed under reduced pressure
  5. customthe solids were partitioned between methylene chloride (500 mL) and water (500 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. custompurified by chromatography on SiO2to

출처 및 근거

ORD 기록
ord-9bb07c05cb8548be8278c6d19ba8869d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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